The subject of this research is C-glycosides. These materials are sometimes found in medicinally active natural products, for example papulacandin (anti-fungal) and altromycin B (anti-tumor). There is also intense interest in C-glycosides as analogs of the more commonly found O-glycosides. If they were to be "faithful" analogs, they could interfere in many natural processes normally reserved for O-glycosides with one major difference. C-glycosides would be stable and have a longer lifetime than inherently unstable and shorter-lived O-glycosides. The study of c_glycosides, in most cases, first requires their synthesis in the laboratory. This will be accomplished using a well-established method invented in 1940, but first recognized as useful for carbohydrate chemistry by the PI in 1997. Thus the Ramberg-Backlund reaction will be used to prepare C-glycoside analogs of daunomycin, a clinically active antitumor agent. The northwest sector of altromycin, a powerful antitumor drug, is a natural C-glycoside which has never been prepared in the lab. This is also a target. Further aims include the synthesis of C-glycolipids as analogs of known, bio-active O-glycolipids including KRN7000, an inducer of NK cells. Another aim of this project is the synthesis of C- glyco analogs of disaccharides which include the sialic acid residue. These materials will mimic O-glycosides involved in adhesion in to both respiratory and gastrointestinal epithelial cells.